Synthesis, Pharmacological, and Hematological Evaluation of Cinnamaldehyde-Derived Schiff Base

Samuel J. Bunu^1,2,4, Oyeintonbara Miediegha¹, Ruth E. Clement¹, Deghinmotei Alfred-Ugbenbo³, Vincent O. Imieje², Cyril O. Usifoh²

Keywords: Schiff base, cinnamaldehyde, para-aminophenol, analgesic, antimicrobial, hematology

DOI: 10.63475/yjm.v4i3.0174

DOI URL: https://doi.org/10.63475/yjm.v4i3.0174

Publish Date: 31-12-2025

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Pages: 596 - 606

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Downloads: 5

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Author Affiliation:

1 Department of Pharmaceutical and Medicinal Chemistry, Faculty of Pharmacy, Niger Delta University, Wilberforce Island, Yenagoa, Bayelsa, Nigeria
2 Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Benin, Benin City, Edo, Nigeria
3 Pharmacist, Department of Pharmaceutical and Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Bayelsa Medical University, Yenagoa, Bayelsa State, Nigeria
4 Drug Analysis and Research Center (DARC), Ebisamdex Global Ventures Ltd., Yenagoa, Bayelsa State, Nigeria

Abstract

Background: Cinnamaldehyde (trans-cinnamaldehyde) and para-aminophenol, (Z)-4-((4-(dimethylamino)benzylidene)-amino)-phenol were used in the synthesis of Schiff base. This study aimed to synthesize and quantify derivatives of para-aminophenol and Cinnamaldehyde Schiff bases derivative, characterize and determine the toxicity and pharmacological properties, as well as potential binding affinity on specific cellular enzymes and proteins.

Methods: The compound was synthesized via microwave-assisted condensation, achieving a high yield of 95.4%, and characterized using physicochemical analysis, thin-layer chromatography

(Rf = 0.69 ± 0.08 in methanol), ¹H NMR (nuclear magnetic resonance), ¹³C NMR, a high-resolution mass spectrometer, and UV-visible spectrophotometry (λmax = 260 nm). Biological evaluations included antimicrobial, acute toxicity (LD₅₀), analgesic, and hematological profiling such as hemoglobin concentration, packed cell volume, platelet count, and differential leukocyte distribution.

Results: The compound demonstrated moderate antimicrobial activity, with zones of inhibition against Escherichia coli (13 mm at 62.5 μg/mL) and Candida albicans (13 mm at 500 μg/mL). The minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) were found to be 250 μg/mL for E. coli and 62.5 μg/mL (MIC) for C. albicans. Analgesic evaluation revealed that the test compound significantly increased reaction time in mice, particularly at 60- and 90-minute post-administration, with effects comparable to pethidine (at a dose of 12 mg/kg). ANOVA confirmed significance (P = 0.0002), while no significant difference was found between the test compound and the standard at peak effect (P = 0.80). LD₅₀ of 1265 mg/kg suggests a moderate toxicity profile. Hematological analysis showed dose-dependent changes in white blood cell and red blood cell counts. In silico docking studies demonstrated a strong binding affinity to key antimicrobial and analgesic targets, including Cyclooxygenase-2 (COX-2) (−7.52 kcal/mol) and 5FSA (−7.65 kcal/mol), which supports the in vivo results.

Conclusions: These findings suggest that the synthesized Schiff base compound has promising potential as a dual-action antimicrobial and analgesic agent, with a relatively safe hematological profile and good molecular interactions at target sites.

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